Table 1. Enantioselective Gold(I)-Catalyzed Addition of Indole to 1,6-Enyne 1a^a.

entry	[Au]	[Ag]	NuH	time (h)	yield (%)b	erc
1	Au1	(R)-Ag6	Indd	44	61	78:22
2	Au2	(R)-Ag6	Indd	44	69	54:46
3	Au3	(R)-Ag6	Indd	44	6	50:50
4	Au4	(R)-Ag6	Indd	44	82	95:5
5	Au5	(R)-Ag6	Indd	44	74	60:40
6	Au6	(R)-Ag6	Indd	44	39	54:46
7	Au4	(S)-Ag6	Indd	44	61	61.5:38.5
8	Au4	(R)-Ag6	EtOHd	14	87	98:2
9	Au4	(S)-Ag6	EtOHd	14	85	57:43
10	Au1	(R)-Ag6	EtOHd	14	67	91:9
11	Au1	(S)-Ag6	EtOHd	14	53	47:53
12	Au1	(R)-Ag1	Inde	14	82	91:9
13	Au4	(R)-Ag1	Inde	14	93	>99:1
14	Au4	(R)-Ag6	Inde	14	98	97.5:2.5
15	Au4	(R)-Ag8	Inde	14	90	95:5
16	Au9	(R)-Ag6	Inde	18	78	94:6
17	Au4		Inde	24	0
18		(R)-Ag1	Inde	24	0
19	Au12	(R)-Ag1	Inde	24	18	52:48
20	Au4	AgSbF6	Inde	24	76	92.5:7.5

^aReactions carried out under Ar or N₂ at a 0.05 mmol scale, at 27 °C with (R)-configured Au(I) complexes.

^bYields determined by ¹H NMR using dodecane as internal standard.

^cer determined by supercritical fluid chromatography (SFC) using a chiral stationary phase.

^dToluene (0.1 M) was used as solvent.

^e1,4-dioxane (0.1 M) was used as solvent. NuH = nucleophile. Ind = Indole.